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Before Jennifer Fleiss joined the boards of Yale Ventures, luxury behemoth Lanvin and photo service Shutterfly, she was a Harvard Business School graduate attempting to start a company with classmate Jennifer Hyman. The year was 2009, and the two aimed to teach consumers to rent designer clothing via subscriptions to a new ecommerce company they called Rent the Runway.\u00a0<\/p>\n
Fleiss acknowledges the significant mental health hurdles she faced throughout her tenure at the New York-based company\u2019s helm, and says that the relationship she shares with cofounder Hyman was vital to helping her persevere.\u00a0<\/p>\n
\u201cThe idea that you\u2019re not in this alone because your cofounder implicitly cares just as much as you do\u2026that\u2019s what kept me afloat in a very sane way amidst losing my mom and having three kids while being at Rent the Runway,\u201d Fleiss said Tuesday in conversation with Bonobos and Pie founder Andy Dunn at Fortune<\/em>\u2019s Brainstorm Tech conference.<\/a>\u00a0<\/p>\n Fleiss, who is now a partner at venture capital fund Initialized Capital and the cofounder of scooter suitcase brand Roll Rider (alongside her three children), grew Rent the Runway into one of the most well-funded consumer brands of 2010s. After launching the company, which lets women rent outfits, dresses, and formalwear made by high-fashion brands and have it delivered to their door, Hyman and Fleiss raised nearly $700 million in venture capital funding. They then grew the company to 1,000-plus employees before a 2021 IPO<\/a>, in which the company began trading at a $1.7 billion valuation<\/a>.\u00a0<\/p>\n The two cofounders implemented biweekly check-ins with each other, where they were \u201cforced to sit down\u201d and chat about their relationship\u2013whether they \u201chad something to talk about or not.\u201d Fleiss, who had a $12 million stake in the company at the time of its IPO, per Forbes<\/em><\/a>, credits this structured accountability for her success and the strength of her partnership with CEO Hyman: \u201cThere was some hard stuff that came up and some funny stuff that came up.\u201d<\/p>\n Though Fleiss transitioned to Rent the Runway\u2019s board in 2017 and took a job as the CEO of Walmart private shopping subsidiary JetBlack (which was shuttered in 2020), she says that she still talks with Hyman daily. Fleiss notes that some of this is business-related, but much of it is \u201clife-related.\u201d<\/p>\n \u201cIn the course of Rent the Runway, what I feel the most proud of is my relationship with Jen [Hyman],\u201d said Fleiss, acknowledging the difficulties the business faced amid the Covid-19 pandemic, when demand for formal outfits all but disappeared. (Around this time the company reported net losses<\/a> of more than $150 million for two consecutive years).<\/p>\n Fleiss reflects on her 16 years building Rent the Runway with Hyman: \u201cThere were so many hard and special moments. Like a spouse\u2013no one lives through that with you in the same way.\u201d<\/p>\n Read more coverage from Brainstorm Tech 2024:<\/em><\/strong><\/p>\n Why Grindr\u2019s CEO believes \u2018synthetic employees\u2019 are about to unleash a brutal talent war for tech startups<\/a><\/p>\n Tech talent and killer powder: The recipe that startups say is fueling the rise of Utah\u2019s Silicon Slopes<\/a><\/p>\n SF Fed Reserve Chief Mary Daly: A.I. replaces tasks, not people<\/a><\/p>\n<\/div>\n CEO Daily provides key context for the news leaders need to know from across the world of business. Every weekday morning, more than 125,000 readers trust CEO Daily for insights about\u2013and from inside\u2013the C-suite. Subscribe Now<\/a>.<\/div>\n<\/div>\nRecommended Newsletter:<\/strong><\/p>\n